


Matchmaker, Matchmaker

by enenfer



Category: Supernatural
Genre: Alternate Universe - College/University, Angst, Anxiety Disorder, Charlie Ships It, Depression, Emotional/Psychological Abuse, Eventual Happy Ending, F/F, F/M, Fluff, Humor, Hurt/Comfort, M/M, Physical Abuse, Smut, Teacher!Dean, artist!Cas, bartender!Dean
Language: English
Status: In-Progress
Published: 2014-06-06
Updated: 2014-06-06
Packaged: 2018-02-03 14:27:53
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 1,936
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1747874
Author URL: https://archiveofourown.org/users/enenfer/pseuds/enenfer
Summary: <blockquote class="userstuff">
              <p>Charlie is on a mission to rekindle Dean and Castiel's three-year-old romance. Turns out playing Matchmaker is just what the doctor ordered.</p>
            </blockquote>





	Matchmaker, Matchmaker

**Author's Note:**

> Hello! My name's Christine and this my attempt at writing a Destiel fanfic! *crosses fingers*

The barista leaned against the granite countertop, her eyes fixated on the beautiful redhead that was sitting by the window. She watched as the hope slowly faded from the woman’s features over the past ten minutes and she wanted nothing more than to make her day a little better. She couldn’t do much, but she figured a free drink was a start. The barista quickly prepared a chai tea latte, humming along to the café’s music while she worked. She handed the money for the drink to one of her coworkers before walking around the counter and approaching the woman.

She sat the steaming cup of tea in front of the woman, flashing her a sympathetic smile. “It’s on the house, sweetheart.”

“Thanks, Gilda. I really appreciate it.”

Gilda gave the woman’s forearm a light squeeze. “It’s not a problem. How late is he?”

“Twenty minutes,” she sighed. “I’m starting to think he flaked out.”

Gilda frowned. “Maybe he just got stuck in traffic. You know how crazy this town is during the summer. Just sit back and relax; he’ll be here before you know it.”

“I hope so.” She huffed out a laugh. “He better show up because he’s really starting to put a damper on my plans.”

“I don’t understand why you’re so keen on playing matchmaker with those two idiots. They had a crush on each other _years_ ago. They probably don’t even remember it, Charlie.”

“They do!” Charlie insisted. “They’re still madly in love with each other and it’s my job to get them back together.”

Gilda rolled her eyes at her girlfriend. “Well I’ve got to get back to work. Good luck and I’ll see you tonight, okay?”

Charlie grabbed Gilda’s hand and kissed her fingers. “Okay. See you tonight, babe.”

Charlie watched Gilda’s retreating form until she was standing behind the counter once more. Then she turned her attention back to the people that were walking past outside. Charlie’s thoughts turned to the man she was about to be reunited with. She hadn’t seen or spoken to him in years. He sounded willing on the phone but knowing him, he was probably taking his sweet time getting his ass over to the café because he was uncomfortable with the whole situation. She didn’t blame him, she just hoped that he would take a leap of faith and show up anyway.

The bell above the door rang a few minutes later, pulling Charlie out of her reverie. Charlie watched as the man approached the counter and began to place his order. She hadn’t even caught a glimpse of his face, and yet she could tell she was looking at the right person. Once his coffee was in his hands, Gilda pointed him in Charlie’s direction.

The man turned towards Charlie, his eyes widening in surprise once he caught a glimpse of his old friend. “Charlie?” the man asked, his voice sounding much deeper than it had on the phone.

Charlie shot up from her seat and closed the distance between them. She pulled him into a tight hug, refusing to let go until she received a hug in return. “I’m so glad to see you, Cas.”

Castiel stepped back, smiling at the sound of his old nickname. “I’m not going to lie, I thought about canceling,” he admitted, running his fingers through his dark hair.

“Well I’m glad you didn’t,” she said, gesturing at her table. Castiel sat in the chair across from Charlie, looking slightly uncomfortable. Again, she didn’t blame him. “We have so much to catch up on.”

Castiel nodded. “Yes we do. How have you been, Charlie?”

“I’ve been great! I just finished my sophomore year, I’m working at a computer repair place in town,” Charlie smiled at Gilda, who was currently wiping down a counter. “And I’m dating _the_ most beautiful barista in the tri-state area.”

Cas smiled down at his drink. He worried his bottom lip between his teeth and sighed. “That’s really great, Charlie. I’m happy for you.”

“What about you, Cas? Are you still in school? Got anyone special in your life?” Charlie waggled her eyebrows as she took a sip of her tea.

“I’m currently enrolled for the following semester here. And no, I don’t have anyone _special_ in my life as of late.”

“As of late? Why? What happened?”

Castiel frowned. “We wanted different things in our relationship. He was very selfish and secretive, and I…I just wanted the truth.”

“I’m so sorry, Cas. But I guess it’s better you figured it out now instead of later.” Charlie leaned back in her chair. “And what about your whole school situation? Weren’t you going to Harvard?”

“Harvard is very expensive,” Castiel sighed, exasperated. “I didn’t have enough money to cover my tuition for another year, so I had no choice but to transfer. Luckily, Anna moved back into town two years ago and she’s letting me stay with her until I can find my own living arrangements.”

“Wow, Charlie said, shaking her head. “Are you and Anna getting along, at least?”

Castiel nodded. “Yes, she had been very understanding ever since she moved out of mother’s house.”

“That’s great, Cas.” Charlie had to fight to keep the smile off her face. It was time to set her little plan into motion. “So do you have any idea of where you wanna live? Are you gonna move into a dorm, an apartment or were you thinking of rooming with a couple people? Sam just moved to California for college and Dean let me move in with him. We have an extra room if you’re interested…”

Castiel’s eyes fluttered open at the sound of his name. A handful of questions entered his mind, none of which Charlie would be able to answer. Instead he opted for the generic, “How…how is he?”

Charlie felt her chest restrict. Castiel just looked so helpless; she wanted to alleviate as much of his sorrow as she could. She reached out and grasped Castiel’s hand firmly. “He’s fine. He misses you, you know. I can tell.”

Castiel tried not to let Charlie’s comment affect him. But it managed to plant itself in Castiel’s mind, spreading its roots all the way to his heart. A flicker of hope began to burn bright in his cerulean eyes. “He does?”

Charlie nodded solemnly. “Do you remember that painting you made for him? The one with the angels falling through the night sky?”

“Yes,” Castiel croaked, needing to take a sip of his coffee to sooth his suddenly dry throat.

“Well he still has it. It’s hanging on the wall in the living room, just above the TV.” Charlie smiled weakly. “I honestly think he stares at _it_ more than he does the TV itself.”

Castiel’s heart began to hammer against his ribcage. “That doesn’t…he can’t…” Castiel’s brain short-circuited, making it impossible for him to form a coherent sentence.

“Cas, I’m telling you the truth. Don’t you believe me?”

“Why, Charlie?” Cas’ words came stumbling out. “After all these years, _why?_ ”

Charlie gave Castiel’s hand a reassuring squeeze, forcing him to look into her eyes. “You left an impression on him, Castiel. I know I’ve only lived with him for a short amount of time, but believe me when I say that you’re still on his mind. He literally hasn’t slept with _anyone_. He just works, goes to school and hangs out with me and Gilda at home.”

“Well it seems like he has become a very well-adjusted man. But that doesn’t mean that he _misses_ me. If I became a part of his life again, I’d just mess everything up…”

“Stop,” Charlie demanded. “You wouldn’t mess anything up! Apart from Sam, I’ve never seen him so happy to be with anyone. He’s just not the same without you in his life, don’t you understand that?”

Castiel honestly couldn’t believe it. The voice in the back of his mind kept telling him that he was unworthy of Dean, that Dean was better off without him. After all these years, Castiel started to believe it. But maybe the voice was wrong? “Charlie…I miss him too.”

Charlie beamed at him, victorious. “Do you want to see him? He’s at home right now.”

“No,” Castiel said, his voice strained. “I can’t…not yet.”

“Too soon?” Castiel nodded; he looked exhausted. “How about this: you take as much time as you need to think things through. If and when you decide that you wanna see Dean again, I’ll convince him to go on a blind date with you. Would you be interested?”

Castiel pursed his lips. “I don’t think that would be wise. If I remember correctly, Dean doesn’t go on dates. If you could convince him to go on a _blind_ date, that would be a miracle.”

Charlie’s smile became wolfish. “You are correct, my friend. But if I talk you up enough, I can convince him to agree to it. Or I’ll just end up irritating him into submission. Whatever comes first.”

“I don’t know,” Castiel sighed. “I’ll have to think about it.”

“Okay. And FYI, Dean bartends at the Roadhouse. Ellen always gives him Monday and Tuesday off. He works nights the rest of the week.” Charlie began to collect her things. “Just in case you wanna avoid him until you’re ready.”

Cas stood up, waiting for Charlie to do the same thing. “Why does he only work nights?”

Charlie chuckled, throwing her purse over her shoulder. “Because every night is ladies night when Dean Winchester is working.”

Castiel couldn’t help but frown. He decidedly ignored the feeling of possessiveness that pooled in the bottom of his stomach. “I’ll call you when I make my decision.”

“You better,” Charlie said as she pulled Castiel into a hug. “And stay in touch, for heaven’s sake.”

Castiel nodded in response, leaving just as quickly as he arrived. Charlie let out a triumphant laugh as she turned towards Gilda.

“Phase one is complete!”

Gilda smirked at her girlfriend. “Great! Now get out of here. You’re scaring the customers.”

Charlie felt a blush creep up her cheeks when she realized she wasn’t the only person in the café. She blew a kiss at her girlfriend before making her exit.

Charlie drove all the way home with a ridiculous smile plastered on her face.

________________________________________

Castiel pulled his Volvo into Anna’s garage, immediately laying his head on the steering wheel. He sat there for a moment, focusing solely on his breathing – in through his nose and out through his mouth. It helped ease the feeling that was clawing its way up his throat but the urge to pull at his hair remained. He cut off the engine, closed the garage door and scrambled into the house.

His vision was black around the edges by that point, threatening to swallow him whole. His pulse hammered in his ears, growing louder with each passing second. He staggered into his bathroom, fumbling to open the orange and white bottle that was sitting on the edge of the sink. He popped two light blue pills into his mouth, deciding to drink straight from the tap. Once he swallowed the pills, Castiel crumpled onto the bathroom floor, his breath sounding harsh in his ears.

By the time Castiel’s heart was beating at a normal pace, the bathroom was flooded with orange light. Cas gripped the edge of the sink, pulling himself to his feet. He staggered into his bedroom and collapsed on his bed. He curled himself into a ball, passing out immediately.

Castiel dreamt of sunlight, freckles and green eyes.

**Author's Note:**

> Constructive criticism is appreciated! Thanks for reading, guys! :)


End file.
